Phillip Wylie Show | Cybersecurity & Pentesting Podcast

What happens when hacking moves beyond computers and into devices that can keep people alive?
In this episode of The Phillip Wylie Show, Phillip Wylie welcomes Sean Satterlee to discuss the rapidly growing field of medical device security. Sean explains how security researchers evaluate connected healthcare technology, the skills needed to transition into hardware hacking, and why traditional pentesting knowledge is still incred...

In this episode of The Phillip Wylie Show, Phillip sits down with longtime friend, former student, and offensive security professional Christian Gonzalez.

Christian shares his journey from curious teenager and network engineer to penetration tester, mobile application security specialist, and AI security researcher.

The conversation explores career growth, certifications, AI security, and how aspiring pentesters can stay relevant i...

In this episode of The Phillip Wylie Show, Phillip Wylie welcomes back cybersecurity leader, content creator, and self-described "Cybersecurity Bestie," Eva Benn. Eva shares her journey from growing up in rural Bulgaria with no access to technology to becoming a cybersecurity leader, red team professional, and influential content creator. The conversation explores how cybersecurity professionals can leverage content creation to edu...

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with legendary application security pioneer and entrepreneur Jeremiah Grossman to discuss the evolution of web security, vulnerability management, cyber insurance, AI-driven software development, and the future of offensive security.Jeremiah shares his hacker origin story, from hacking his ISP as a teenager to discovering vulnerabilities in Yahoo Mail during the ear...

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with legendary security expert Ed Skoudis to discuss his hacker origin story, the evolution of penetration testing, and how AI is transforming offensive security.
Ed shares how he got started hacking on early home computers like the Commodore VIC-20 and Timex Sinclair 1000, his journey into professional penetration testing, and the early days of DEF CON and the c...

Computer security analyst and author Winn Schwartau joins Phillip Wylie for a deep conversation on hacker culture, cognitive security, information warfare, and the evolution of cybersecurity from the early days of computing to today’s AI-driven world.
Winn shares stories from his early days bypassing locked telephone systems as a child, his transition from the live recording industry into cybersecurity in the 1980s, and ho...

In this episode of The Phillip Wylie Show, Phillip sits down with Amar Sonik to talk about what really matters in cybersecurity.
They dig into why fundamentals like networking and Linux still separate good security professionals from great ones, how conferences like B-Sides Singapore and CYBR.HAK.CON. help shape careers, and how AI is changing the way people learn hacking.
Amar Sonik shares practical advice for anyone trying ...

In this episode of The Phillip Wylie Show, Phillip sits down with Zach Tackett, a listener-turned-guest who carved his path into cybersecurity and pentesting through persistence, hands-on learning, and networking.
Zach shares his unconventional journey from a blue-collar upbringing and early struggles with asthma to discovering programming, cybersecurity, and ultimately landing roles supporting NASA and later becoming a security...

In this episode of The Phillip Wylie Show, Phillip sits down with Marie Hamilton to explore her unconventional and inspiring path into cybersecurity. From early curiosity about computers and creative problem-solving as a teenager to serving in the military, navigating career pivots, and ultimately launching her own cybersecurity and investigations business, Marie shares a candid look at her journey.
They discuss the realities of...

How do you go from professional wrestling and powerlifting to a career in cybersecurity and penetration testing?

In this special solo episode of The Phillip Wylie Show, Phillip Wylie shares his personal hacker origin story and the unconventional path that led him from wrestling matches and construction jobs to becoming a penetration tester, security evangelist, author, and podcast host.

If you're trying to break into cybersec...

In this episode of The Phillip Wylie Show, host Phillip Wylie sits down with offensive security professional Jamy Casteel to discuss his journey from small-town IT technician to penetration tester and red teamer. Jamy shares how an early exposure to social engineering and physical pentesting sparked his interest in security and shaped his career path.
The conversation explores the differences between pentesting and red teaming, ...

In this episode of the Phillip Wylie Show, host Phillip Wylie sits down with cybersecurity professional Travis Stein to discuss practical strategies for breaking into cybersecurity, building technical skills, and advancing from IT into security roles. Travis shares his journey from help desk roles into cybersecurity engineering and offers actionable advice for aspiring professionals looking to stand out in a competitive field.
T...

In this episode, Phillip Wylie sits down with Dr. Gregory Carpenter to explore his journey from early childhood curiosity to a distinguished career in cybersecurity, military operations, and advanced threat modeling.

Greg shares how his early interest in security evolved from physical lockpicking and unconventional problem solving into work involving digital security, NSA operations, and space-related missions.

The conversation dive...

In this episode of the Phillip Wylie Show, Allie Mellen shares her journey from a computer engineering student to a cybersecurity expert and industry analyst.

She discusses the importance of hands-on experience in cybersecurity, the evolution of cybersecurity tools, and the significance of a hacker mindset.

Allie also emphasizes the need for clear communication in cybersecurity for non-technical audiences and provides advice on sel...

In this episode of the Phillip Wylie Show, host Phillip Wylie speaks with Eve Maler, a prominent figure in identity security.

They discuss the importance of community in cybersecurity, Eve's journey into the field, the evolution of identity technologies like SAML and OAuth, advancements in authentication methods, and the impact of AI on identity management.

Eve also shares insights from her upcoming book on digital identity, emphas...

In this episode, Sudhanshu Chauhan discusses the transformative impact of AI on the cybersecurity landscape. He explains how AI has introduced new attack vectors and the dual nature of AI in cybersecurity, serving both as a tool for attacks and as a target for attacks.

The conversation emphasizes the need for security professionals to adapt to these changes and explore innovative approaches to penetration testing and security measu...

In this episode of the Phillip Wylie Show, Dorota Kozlowska shares her inspiring journey from a hesitant high school student to a successful professional in offensive security and content creation.

She discusses her challenges in breaking into the male-dominated field of cybersecurity, her passion for pen testing, and her commitment to empowering other women in tech through her podcast, 'The Woman in Red.'

Dorota emphasizes the imp...

In this episode of the Phillip Wylie Show, host Phillip Wylie welcomes cybersecurity expert Keelan Knox, who shares his fascinating hacker origin story.

Keelan recounts his early curiosity about technology, which led him to dismantle various devices and eventually discover the world of hacking and cybersecurity. He emphasizes the importance of social engineering in the field and how it became a natural skill for him.

The conversati...

In this episode of The Phillip Wylie Show, Phillip Wylie sits down with Michael Farnum and Sam Van Ryder to discuss the growth of CYBR.SEC.Community, formerly known as HOU.SEC.CON. They share their hacker origin stories and how a grassroots conference evolved into a national, community-driven cybersecurity movement.

The conversation covers the expansion of CYBR.SEC.Community to include OT.SEC.CON, EXEC.SEC.CON, YOUTH.SEC.CON, CYBR.H...